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Molecules 2010, 15(12), 9403-9417; doi:10.3390/molecules15129403
Article

Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis

1,* , 2, 2,3 and 4,5,6
1 Women Students-Medical Studies and Sciences Sections, Chemistry Department, College of Science, King Saud University, P.O. Box 22452, Riyadh 11495, Saudi Arabia 2 Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia 3 Chemistry Department, Faculty of Science, Alexandria University, 426 Ibrahimia, 21321 Alexandria, Egypt 4 Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, Barcelona 08028, Spain 5 CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, Barcelona 08028, Spain 6 Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, Barcelona 08028, Spain
* Author to whom correspondence should be addressed.
Received: 29 November 2010 / Revised: 14 December 2010 / Accepted: 15 December 2010 / Published: 20 December 2010
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Abstract

A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid derivatives as a major product. The oxyma (ethyl 2-cyano-2-(hydroxyimino)acetate) uronium salt was superior to other uronium salts in terms of racemization, while 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT, 9) gave the best results.
Keywords: coupling reagents; triazinyloximino derivatives; solution phase peptide synthesis; uronium salt; racemization coupling reagents; triazinyloximino derivatives; solution phase peptide synthesis; uronium salt; racemization
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Al-Warhi, T.I.; AL-Hazimi, H.M.; El-Faham, A.; Albericio, F. Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis. Molecules 2010, 15, 9403-9417.

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